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So, if two guards have Jake between them, and at the beginning of the scene, Jake is unconscious, his body would be hanging slack between them, lower than their waistline.  Any striking to be done would be below the guard’s waistline with Jake’s body angled down to a slant to the floor.  A knee to the stomach would require one of the guards to release his hold, pivot towards Jake’s body, face him, which would cause Jake to slump even lower. To strike him with a knee, the guard would have to use his non-weight bearing leg.  The hit would more than likely strike him in the solar plexus bone or ribs, rather than the stomach.  It would be an awkward move.

Think about it.  The guards would be dragging him by his arms, probably with their forearms under his armpits, if they are not just dragging him by his arms alone.  I would think the guards would not want the bulk of his body dragging the ground, because that would make him harder to pull forward, so he would be lifted enough so that only his feet are dragging, as you described.  My sense is, the guards just want to pitch him into a locked cell and have done with him, as soon as possible with the least amount of trouble.

In a two person carry scenario, as you’ve described, the victim is either held up between the two carriers with his arms around their necks and shoulders or he is dragged under his armpits with his hands bound behind his back.  The latter is the more probable because this is the posture of a prisoner. Why wouldn’t they bind him unless they are overconfident?  Doesn’t Jake have a known history of duplicity and eluding capture?  I would think so.  They would already expect him to struggle when he came to.  To hold his dead weight, each of the guard’s inner arms would be occupied, and they would only be able to strike him with their outer arms.  For each guard, this would be a cross body strike, lacking force or momentum, unless they struck him with a gat, baton, or Billy club.  Those would be downward strikes, hitting the top of his head or shoulders, but the guards would have to drop him and pivot to face him to do it.

What would make more sense and have cruelty about it is merely to drop him and let him hit the ground and faceplant.  With his arms bound behind him, he could not catch himself and stop his face and chin from striking the floor.  It would be a stunning blow and quite possibly break his nose, making him much more “cooperative” in the process.

If Jake is smart, he would most likely feign that he is still unconscious with surreptitious glances to try to make sense of where he is being taken, so he could calculate an escape route.

Punching someone is either an uppercut motion or a horizontal motion, requiring the head to be above or on the same plane as the swinging or cocked fist.  A knee to the stomach requires the striking knee to be lower than the gut area, but not angled away from it.  It is a low arc moving slightly forward but forcibly upward, with the victim falling forward and downward into the strike.